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Three L-hydroxylysine structures have been determined at 100 K by single-crystal X-ray diffraction. High-resolution data using either a laboratory or synchrotron source were collected and subjected to invariom- and independent atom-model (IAM) refinements. Anisotropic displacement parameters (ADPs) obtained from invariom refinement were compared (i) with results from a full multipole and (ii) with an IAM high-order refinement. Differences were visualized with the program PEANUT and were complemented by quantitative results from a Hirshfeld test. Influences of scale factor differences, and of refinement against F^2 versus F, have been investigated. Systematic errors were observed in the IAM, especially when only low-order data were available. Although these errors were reduced in high-order IAM refinements, they only disappeared in charge density - and likewise - invariom refinements.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108032163/ws5058sup1.cif
Contains datablocks I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108032163/ws5058Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108032163/ws5058IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108032163/ws5058IIIsup4.hkl
Contains datablock III

CCDC references: 718181; 718182; 718183

Computing details top

Data collection: Bruker AXS APEX2, 2006 for (I); CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) for (II), (III). Cell refinement: Bruker AXS APEX2 2006 for (I); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) for (II), (III). Data reduction: Bruker AXS APEX2 2006 for (I); CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) for (II), (III). Program(s) used to solve structure: SHELXS (Sheldrick, 1997) for (I). For all compounds, program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).

(I) top
Crystal data top
C6H15N2O3·ClF(000) = 424.0
Mr = 198.65Dx = 1.428 Mg m3
Orthorhombic, P212121Synchrotron radiation, λ = 0.4750 Å
Hall symbol: P 2ac 2abCell parameters from 38562 reflections
a = 5.4315 (1) Åθ = 2.4–39.9°
b = 9.8019 (1) ŵ = 0.39 mm1
c = 17.3505 (2) ÅT = 100 K
V = 923.72 (2) Å3Rectangle, colorless
Z = 40.19 × 0.18 × 0.11 mm
Data collection top
Bruker D8
diffractometer
10455 independent reflections
Radiation source: synchrotron9078 reflections with F > 3u(F)
Si (111) monochromatorθmax = 40.0°, θmin = 1°
ω scansh = 1414
Absorption correction: empirical (using intensity measurements)
SADABS (Version 05/2007), G. S. Sheldrick, 2007
k = 2626
Tmin = 0.655, Tmax = 0.748l = 4646
232425 measured reflections
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.034 w1 = 1/[s2(Fo)]
S = 1.90(Δ/σ)max < 0.001
9078 reflectionsΔρmax = 1.67 e Å3
169 parametersΔρmin = 0.28 e Å3
Special details top

Geometry. As part of the invariom modelling procedure bond distances to hydrogen atoms were set to values from geometry optimizations of model compounds that mimick the chemical environment of the hydrogen atom. These values are very similar to bond distances obtained from neutron diffraction.

Refinement. Refinement was performed on F with the program XDLSM. Hydrogen atom positions were obtained by elongating the bond length along the vector of the atom they are attached to and their refined positions from the independent atom model. The following dummy atoms were used: DUM0 0 0 0 0 0 DUM1 0.07212 - 0.02361 - 0.02848 0 0 DUM2 - 0.05429 0.11225 0.01976 0 0 The Flack-parameter was not refined since the anomalous signal was deemed to be absend for the synchrotron radiation used. The X—H bond lengths using conventional scattering factors are usually 10% too short when compared to results from neutron diffraction. In invariom modelling this error is significantly reduced by the non-spherical scattering factors. The highest residual peak is next the the heaviest atom and disappears when the high resolution is reduced.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
CL(1)0.44577 (2)0.386220 (10)0.288400 (10)0.01
O(1)0.44924 (7)0.00531 (4)0.13983 (2)0.013
O(2)0.39641 (6)0.19193 (4)0.06884 (2)0.011
O(3)0.30706 (5)0.12897 (4)0.09962 (2)0.011
N(1)0.09186 (6)0.18791 (4)0.07872 (2)0.008
N(2)0.04153 (7)0.26456 (4)0.21651 (2)0.01
C(1)0.31669 (6)0.08753 (4)0.10341 (2)0.008
C(2)0.03884 (6)0.06002 (4)0.10053 (2)0.008
C(3)0.02906 (7)0.05632 (4)0.04541 (2)0.009
C(4)0.06789 (7)0.04238 (4)0.03728 (2)0.009
C(5)0.04951 (7)0.15102 (4)0.08924 (2)0.008
C(6)0.08080 (7)0.15998 (5)0.16687 (3)0.01
H(3)0.31610.048140.130870.024 (5)
H(1A)0.055670.264190.117420.025 (4)
H(1B)0.275280.163870.080280.026 (5)
H(1C)0.059930.214550.022490.017 (4)
H(2A)0.049510.356680.188880.033 (6)
H(2B)0.053590.285860.266060.018 (4)
H(2C)0.209020.237470.238890.027 (5)
H(2)0.010890.031110.159970.025 (4)
H(3A)0.046230.150710.069450.024 (4)
H(3B)0.230080.059920.041180.018 (4)
H(4A)0.268970.04820.034340.028 (5)
H(4B)0.029940.056850.06360.014 (3)
H(5)0.032840.250130.060150.020 (4)
H(6A)0.08530.06060.196260.016 (3)
H(6B)0.276580.187690.162410.021 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
CL(1)0.00947 (2)0.01179 (3)0.00970 (3)0.00066 (3)0.00000 (2)0.00086 (2)
O(1)0.00746 (7)0.01443 (11)0.01577 (11)0.00140 (8)0.00103 (8)0.00588 (9)
O(2)0.00687 (6)0.01125 (10)0.01419 (11)0.00097 (7)0.00021 (7)0.00398 (8)
O(3)0.00684 (6)0.01132 (11)0.01345 (10)0.00011 (7)0.00032 (7)0.00038 (7)
N(1)0.00628 (6)0.00889 (9)0.01013 (9)0.00039 (7)0.00020 (6)0.00017 (7)
N(2)0.00982 (8)0.01146 (10)0.00999 (10)0.00138 (8)0.00028 (8)0.00064 (7)
C(1)0.00570 (7)0.00949 (11)0.00886 (10)0.00008 (7)0.00020 (7)0.00103 (8)
C(2)0.00593 (7)0.00885 (10)0.00845 (9)0.00016 (8)0.00023 (7)0.00056 (7)
C(3)0.00794 (9)0.00855 (10)0.01008 (11)0.00084 (8)0.00072 (8)0.00005 (8)
C(4)0.00833 (9)0.00933 (11)0.01026 (11)0.00138 (8)0.00090 (8)0.00091 (8)
C(5)0.00740 (8)0.00813 (9)0.00992 (10)0.00010 (8)0.00015 (8)0.00042 (7)
C(6)0.00853 (9)0.01060 (12)0.01115 (12)0.00148 (9)0.00099 (8)0.00110 (9)
Geometric parameters (Å, º) top
O(1)—C(1)1.2518 (5)C(2)—H(2)1.1032
O(2)—C(1)1.2627 (5)C(3)—C(4)1.5345 (6)
O(3)—C(5)1.4269 (5)C(3)—H(3A)1.0941
O(3)—H(3)0.9614C(3)—H(3B)1.0948
N(1)—H(1A)1.0239C(4)—C(5)1.5340 (6)
N(1)—H(1B)1.0241C(4)—H(4A)1.0948
N(1)—H(1C)1.0248C(4)—H(4B)1.0941
N(2)—H(2A)1.0233C(5)—C(6)1.5241 (6)
N(2)—H(2B)1.0245C(5)—H(5)1.0985
N(2)—H(2C)1.0241C(6)—H(6A)1.0997
C(1)—C(2)1.5339 (5)C(6)—H(6B)1.1003
C(2)—C(3)1.5333 (6)
C(5)—O(3)—H(3)104.25C(4)—C(3)—H(3B)106.41
H(1A)—N(1)—H(1B)109.72H(3A)—C(3)—H(3B)111.78
H(1A)—N(1)—H(1C)113.94C(3)—C(4)—C(5)110.18 (3)
H(1B)—N(1)—H(1C)104.38C(3)—C(4)—H(4A)107.10
H(2A)—N(2)—H(2B)103.57C(3)—C(4)—H(4B)113.87
H(2A)—N(2)—H(2C)111.64C(5)—C(4)—H(4A)113.95
H(2B)—N(2)—H(2C)100.52C(5)—C(4)—H(4B)107.08
O(1)—C(1)—O(2)124.35 (4)H(4A)—C(4)—H(4B)104.70
O(1)—C(1)—C(2)117.98 (4)O(3)—C(5)—C(4)112.12 (3)
O(2)—C(1)—C(2)117.67 (3)O(3)—C(5)—C(6)110.63 (3)
C(1)—C(2)—C(3)112.81 (3)O(3)—C(5)—H(5)105.83
C(1)—C(2)—H(2)104.81C(4)—C(5)—C(6)111.49 (3)
C(3)—C(2)—H(2)109.46C(4)—C(5)—H(5)108.04
C(2)—C(3)—C(4)115.75 (3)C(6)—C(5)—H(5)108.47
C(2)—C(3)—H(3A)107.53C(5)—C(6)—H(6A)111.66
C(2)—C(3)—H(3B)107.80C(5)—C(6)—H(6B)113.64
C(4)—C(3)—H(3A)107.67H(6A)—C(6)—H(6B)103.28
(II) top
Crystal data top
C6H16N2O3·2(Cl)F(000) = 248.0
Mr = 235.11Dx = 1.366 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ybCell parameters from 16801 reflections
a = 8.6224 (2) Åθ = 2.8–57.4°
b = 7.0489 (2) ŵ = 0.55 mm1
c = 9.8061 (2) ÅT = 100 K
β = 106.486 (2)°Rectangle, colorless
V = 571.50 (3) Å30.37 × 0.25 × 0.22 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur S
diffractometer
9042 independent reflections
Radiation source: Enhance (Mo) X-ray Source6540 reflections with F > 3u(f)
Graphite monochromatorRint = 0.036
Detector resolution: 16.0009 pixels mm-1θmax = 45.3°, θmin = 2.8°
ω scansh = 1717
Absorption correction: analytical
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
k = 1414
Tmin = 0.878, Tmax = 0.916l = 1919
29885 measured reflections
Refinement top
Refinement on FH-atom parameters constrained
Least-squares matrix: full w1 = 1/[s2(Fo)]
R[F2 > 2σ(F2)] = 0.023(Δ/σ)max < 0.001
wR(F2) = 0.018Δρmax = 0.60 e Å3
S = 1.73Δρmin = 0.25 e Å3
6540 reflectionsAbsolute structure: (Dittrich et al., 2006)
181 parametersAbsolute structure parameter: 0.00 (2)
0 restraints
Special details top

Geometry. As part of the invariom modelling procedure bond distances to hydrogen atoms were set to values from geometry optimizations of model compounds that mimick the chemical environment of the hydrogen atom. These values are very similar to bond distances obtained from neutron diffraction.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
CL(1)0.68112 (2)0.745660.88733 (2)0.018
CL(2)0.65514 (2)0.26022 (4)0.58001 (2)0.018
O(1)0.16852 (8)0.93309 (10)0.91323 (7)0.029
O(2)0.36093 (5)0.75261 (12)1.05516 (5)0.02
O(3)0.24657 (6)0.33080 (8)0.48082 (5)0.018
N(1)0.35366 (7)0.49854 (10)0.84942 (7)0.017
N(2)0.31376 (8)0.06809 (10)0.66336 (7)0.018
C(1)0.26032 (8)0.77895 (11)0.94447 (7)0.016
C(2)0.22081 (8)0.64061 (11)0.82109 (8)0.015
C(3)0.05566 (8)0.54548 (12)0.80251 (8)0.016
C(4)0.01243 (9)0.46390 (13)0.65301 (8)0.017
C(5)0.17532 (8)0.36406 (11)0.62835 (8)0.014
C(6)0.15640 (8)0.17076 (12)0.70019 (9)0.018
H(1)0.21321.023180.987340.031 (3)
H(3)0.290360.449610.439780.025 (3)
H(1A)0.360360.423240.94010.028 (3)
H(1B)0.463560.564120.869470.023 (3)
H(1C)0.341220.41580.761280.034 (3)
H(2A)0.413050.153030.650970.030 (3)
H(2B)0.320680.033330.736020.038 (4)
H(2C)0.335340.001060.568130.027 (3)
H(2)0.220690.714120.722170.026 (3)
H(3A)0.067520.438720.885720.037 (3)
H(3B)0.029880.651010.81930.032 (3)
H(4A)0.075450.371790.624720.026 (3)
H(4B)0.028310.583020.579090.030 (3)
H(5)0.26060.448880.667480.023 (3)
H(6A)0.072360.080050.664170.036 (3)
H(6B)0.112950.185350.816470.034 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
CL(1)0.02086 (7)0.01358 (7)0.01903 (7)0.00007 (8)0.00780 (5)0.00216 (8)
CL(2)0.01903 (6)0.01614 (8)0.01750 (7)0.00180 (8)0.00391 (5)0.00263 (8)
O(1)0.0291 (3)0.0192 (3)0.0321 (3)0.0082 (2)0.0070 (2)0.0078 (3)
O(2)0.0240 (2)0.0161 (2)0.0156 (2)0.0016 (3)0.0003 (2)0.0031 (3)
O(3)0.0203 (2)0.0157 (2)0.0148 (2)0.0015 (2)0.0020 (2)0.0010 (2)
N(1)0.0160 (3)0.0162 (3)0.0160 (3)0.0001 (2)0.0044 (2)0.0024 (2)
N(2)0.0193 (3)0.0154 (3)0.0184 (3)0.0003 (2)0.0057 (2)0.0028 (2)
C(1)0.0164 (2)0.0118 (4)0.0190 (3)0.0007 (2)0.0038 (2)0.0013 (3)
C(2)0.0148 (3)0.0140 (3)0.0138 (3)0.0009 (2)0.0026 (2)0.0011 (2)
C(3)0.0144 (3)0.0178 (4)0.0152 (3)0.0017 (2)0.0031 (2)0.0021 (3)
C(4)0.0152 (3)0.0205 (4)0.0144 (3)0.0029 (3)0.0034 (2)0.0014 (3)
C(5)0.0131 (3)0.0143 (3)0.0137 (3)0.0000 (2)0.0030 (2)0.0004 (2)
C(6)0.0162 (3)0.0172 (3)0.0185 (3)0.0011 (2)0.0036 (2)0.0036 (3)
Geometric parameters (Å, º) top
O(1)—C(1)1.3279 (9)C(2)—C(3)1.5373 (10)
O(1)—H(1)0.9596C(2)—H(2)1.0995
O(2)—C(1)1.1962 (8)C(3)—C(4)1.5284 (10)
O(3)—C(5)1.4216 (9)C(3)—H(3A)1.0933
O(3)—H(3)0.9590C(3)—H(3B)1.0925
N(1)—H(1A)1.0230C(4)—C(5)1.5276 (10)
N(1)—H(1B)1.0221C(4)—H(4A)1.0918
N(1)—H(1C)1.0229C(4)—H(4B)1.0922
N(2)—H(2A)1.0233C(5)—C(6)1.5213 (10)
N(2)—H(2B)1.0229C(5)—H(5)1.0979
N(2)—H(2C)1.0226C(6)—H(6A)1.0973
C(1)—C(2)1.5155 (10)C(6)—H(6B)1.0994
C(1)—O(1)—H(1)106.37C(4)—C(3)—H(3B)107.98
C(5)—O(3)—H(3)106.74H(3A)—C(3)—H(3B)106.28
H(1A)—N(1)—H(1B)104.29C(3)—C(4)—C(5)114.25 (6)
H(1A)—N(1)—H(1C)113.90C(3)—C(4)—H(4A)111.23
H(1B)—N(1)—H(1C)106.83C(3)—C(4)—H(4B)106.80
H(2A)—N(2)—H(2B)106.23C(5)—C(4)—H(4A)111.04
H(2A)—N(2)—H(2C)103.95C(5)—C(4)—H(4B)108.22
H(2B)—N(2)—H(2C)105.75H(4A)—C(4)—H(4B)104.70
O(1)—C(1)—O(2)124.59 (7)O(3)—C(5)—C(4)110.45 (6)
O(1)—C(1)—C(2)110.98 (6)O(3)—C(5)—C(6)106.39 (6)
O(2)—C(1)—C(2)124.43 (7)O(3)—C(5)—H(5)107.85
C(1)—C(2)—C(3)111.47 (6)C(4)—C(5)—C(6)111.49 (6)
C(1)—C(2)—H(2)110.17C(4)—C(5)—H(5)111.76
C(3)—C(2)—H(2)109.40C(6)—C(5)—H(5)108.69
C(2)—C(3)—C(4)111.63 (6)C(5)—C(6)—H(6A)111.51
C(2)—C(3)—H(3A)108.94C(5)—C(6)—H(6B)110.90
C(2)—C(3)—H(3B)109.11H(6A)—C(6)—H(6B)109.06
C(4)—C(3)—H(3A)112.71
(III) top
Crystal data top
C6H16N2O3·H2O·2(Cl)Z = 1
Mr = 253.12F(000) = 134.00
Triclinic, P1Dx = 1.436 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.7107 Å
a = 5.4491 (3) ÅCell parameters from 34253 reflections
b = 7.3962 (4) Åθ = 2.6–51.4°
c = 8.1337 (4) ŵ = 0.55 mm1
α = 79.382 (4)°T = 100 K
β = 73.191 (5)°Rectangle, colorless
γ = 69.544 (5)°0.44 × 0.40 × 0.18 mm
V = 292.75 (3) Å3
Data collection top
Oxford Diffraction Xcalibur S
diffractometer
12708 independent reflections
Radiation source: Enhance (Mo) X-ray Source10693 reflections with F > 3u(F)
Graphite monochromatorRint = 0.022
Detector resolution: 16.0009 pixels mm-1θmax = 51.4°, θmin = 2.6°
ω scansh = 1111
Absorption correction: analytical
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
k = 1616
Tmin = 0.845, Tmax = 0.924l = 1717
45855 measured reflections
Refinement top
Refinement on FH-atom parameters constrained
Least-squares matrix: full w1 = 1/[s2(Fo)]
R[F2 > 2σ(F2)] = 0.020(Δ/σ)max < 0.001
wR(F2) = 0.019Δρmax = 0.70 e Å3
S = 1.73Δρmin = 0.23 e Å3
10693 reflectionsAbsolute structure: (Dittrich et al., 2006c)
190 parametersAbsolute structure parameter: 0.03 (1)
0 restraints
Special details top

Geometry. As part of the invariom modelling procedure bond distances to hydrogen atoms were set to values from geometry optimizations of model compounds that mimick the chemical environment of the hydrogen atom. These values are very similar to bond distances obtained from neutron diffraction.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
CL(1)0.806990.22660.152540.017
CL(2)0.73962 (3)0.55375 (2)0.62145 (2)0.016
O(1)1.30652 (8)0.53581 (7)1.04021 (5)0.02
O(2)1.24225 (8)0.35346 (7)1.25037 (5)0.021
O(3)0.78915 (8)0.03575 (6)0.60225 (5)0.016
O(1W)0.21638 (8)0.07649 (7)0.38356 (5)0.019
N(1)0.71901 (8)0.18568 (7)1.26703 (5)0.014
N(2)0.37616 (8)0.32178 (7)0.55969 (5)0.014
C(1)1.16180 (9)0.40042 (7)1.14575 (6)0.013
C(2)0.87696 (9)0.30458 (7)1.11993 (5)0.012
C(3)0.88502 (9)0.18022 (7)0.94660 (5)0.013
C(4)0.60511 (9)0.06778 (8)0.91499 (5)0.013
C(5)0.62716 (9)0.06783 (7)0.74930 (5)0.012
C(6)0.34985 (9)0.18560 (8)0.71956 (6)0.015
H(1)1.473280.602171.073270.034 (3)
H(3)0.767760.161950.621690.024 (3)
H(1A)0.73810.265471.382110.022 (2)
H(1B)0.515890.132311.276280.035 (3)
H(1C)0.775320.064931.255520.030 (3)
H(2A)0.47270.413620.570520.037 (3)
H(2B)0.192220.413840.545130.025 (3)
H(2C)0.463620.244330.454310.019 (2)
H(2)0.783320.416331.126310.025 (2)
H(3A)0.991430.077790.941610.029 (3)
H(3B)0.999220.280770.847790.025 (2)
H(4A)0.500960.167960.909510.028 (2)
H(4B)0.477960.023971.018520.018 (2)
H(5)0.731940.16960.751420.029 (3)
H(6A)0.254310.087040.696920.028 (3)
H(6B)0.227260.267540.83110.036 (3)
H(1W)0.093770.027030.475760.042 (3)
H(2W)0.130950.152690.294190.038 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
CL(1)0.01395 (4)0.01147 (5)0.02175 (5)0.00312 (4)0.00709 (4)0.00072 (4)
CL(2)0.01591 (5)0.01369 (5)0.01557 (4)0.00602 (4)0.00587 (3)0.00126 (3)
O(1)0.01300 (10)0.0200 (2)0.0227 (2)0.00080 (10)0.00680 (10)0.00890 (10)
O(2)0.01350 (10)0.0232 (2)0.02230 (10)0.00130 (10)0.00870 (10)0.00860 (10)
O(3)0.01720 (10)0.0146 (2)0.01240 (10)0.00380 (10)0.00130 (10)0.00020 (10)
O(1W)0.01180 (10)0.0224 (2)0.02040 (10)0.00460 (10)0.00400 (10)0.00400 (10)
N(1)0.01230 (10)0.0128 (2)0.01190 (10)0.00180 (10)0.00200 (10)0.00010 (10)
N(2)0.01410 (10)0.0123 (2)0.01390 (10)0.00380 (10)0.00590 (10)0.00090 (10)
C(1)0.00980 (10)0.0113 (2)0.01360 (10)0.00190 (10)0.00370 (10)0.00150 (10)
C(2)0.00980 (10)0.0109 (2)0.01250 (10)0.00270 (10)0.00370 (10)0.00010 (10)
C(3)0.01070 (10)0.0144 (2)0.01130 (10)0.00290 (10)0.00340 (10)0.00070 (10)
C(4)0.01100 (10)0.0146 (2)0.01130 (10)0.00340 (10)0.00370 (10)0.00090 (10)
C(5)0.01100 (10)0.0111 (2)0.01200 (10)0.00350 (10)0.00410 (10)0.00010 (10)
C(6)0.01150 (10)0.0163 (2)0.01320 (10)0.00420 (10)0.00460 (10)0.00190 (10)
Geometric parameters (Å, º) top
O(1)—C(1)1.3164 (6)C(2)—C(3)1.5329 (6)
O(1)—H(1)0.9595C(2)—H(2)1.0999
O(2)—C(1)1.2121 (5)C(3)—C(4)1.5319 (6)
O(3)—H(3)0.9596C(3)—H(3A)1.0926
O(1W)—H(1W)0.9597C(3)—H(3B)1.0919
O(1W)—H(2W)0.9618C(4)—C(5)1.5259 (6)
N(1)—H(1A)1.0224C(4)—H(4A)1.0926
N(1)—H(1B)1.0216C(4)—H(4B)1.0920
N(1)—H(1C)1.0221C(5)—C(6)1.5217 (6)
N(2)—H(2A)1.0221C(5)—H(5)1.0972
N(2)—H(2B)1.0220C(6)—H(6A)1.0985
N(2)—H(2C)1.0211C(6)—H(6B)1.0972
C(1)—C(2)1.5235 (6)
C(1)—O(1)—H(1)107.84C(2)—C(3)—H(3B)105.83
H(1W)—O(1W)—H(2W)112.00C(4)—C(3)—H(3A)109.06
H(1A)—N(1)—H(1B)105.21C(4)—C(3)—H(3B)109.62
H(1A)—N(1)—H(1C)110.66H(3A)—C(3)—H(3B)109.86
H(1B)—N(1)—H(1C)104.13C(3)—C(4)—C(5)110.78 (4)
H(2A)—N(2)—H(2B)103.03C(3)—C(4)—H(4A)110.32
H(2A)—N(2)—H(2C)115.03C(3)—C(4)—H(4B)111.64
H(2B)—N(2)—H(2C)107.50C(5)—C(4)—H(4A)110.53
O(1)—C(1)—O(2)125.06 (4)C(5)—C(4)—H(4B)106.16
O(1)—C(1)—C(2)111.94 (4)H(4A)—C(4)—H(4B)107.20
O(2)—C(1)—C(2)122.94 (5)C(4)—C(5)—C(6)111.33 (4)
C(1)—C(2)—C(3)110.09 (4)C(4)—C(5)—H(5)111.93
C(1)—C(2)—H(2)109.65C(6)—C(5)—H(5)107.91
C(3)—C(2)—H(2)110.82C(5)—C(6)—H(6A)108.96
C(2)—C(3)—C(4)113.65 (4)C(5)—C(6)—H(6B)109.65
C(2)—C(3)—H(3A)108.65H(6A)—C(6)—H(6B)111.67
 

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